title: Synthesis, antibacterial activities, and 3D-QSAR of sulfone derivatives containing 1, 3, 4-oxadiazole moiety.
abstract: A series of sulfone derivatives containing 1, 3, 4-oxadiazole moiety were prepared and evaluated for their antibacterial activities by the turbidimeter test. Most compounds inhibited growth of Ralstonia solanacearum (R. solanacearum) from tomato and tobacco bacterial wilt with high potency, among which compounds 5a and 5b exhibited the most potent inhibition against R. solanacearum from tomato and tobacco bacterial wilts with EC50 values of 19.77 and 8.29 μg/mL, respectively. Our results also demonstrated that 5a, 5b, and a number of other compounds were more potent than commercial bactericides Kocide 3000 and Thiodiazole Copper, which inhibited R. solanacearum from tomato bacterial wilt with EC50 values of 93.59 and 99.80 μg/mL and tobacco bacterial wilt with EC50 values of 45.91 and 216.70 μg/mL, respectively. The structure-activity relationship (SAR) of compounds was studied using three-dimensional quantitative structure-activity relationship (3D-QSAR) models created by comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) based on compound bioactivities against tomato and tobacco bacterial wilts. The 3D-QSAR models effectively predicted the correlation between inhibitory activity and steric-electrostatic properties of compounds.
authors.affiliation: State Key Laboratory Breeding Base of Blue Pesticide and Agricultural Bioengineering, Key Laboratory of Blue Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Huaxi District, Guiyang, 550025, China.
authors.forename: Pei
authors.initials: P
authors.lastname: Li
authors.forename: Juan
authors.initials: J
authors.lastname: Yin
authors.forename: Weiming
authors.initials: W
authors.lastname: Xu
authors.forename: Jian
authors.initials: J
authors.lastname: Wu
authors.forename: Ming
authors.initials: M
authors.lastname: He
authors.forename: Deyu
authors.initials: D
authors.lastname: Hu
authors.forename: Song
authors.initials: S
authors.lastname: Yang
authors.forename: Baoan
authors.initials: B
authors.lastname: Song
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016018:Least-Squares Analysis; D018551:Solanum lycopersicum / Q000382:microbiology; D010069:Oxadiazoles / Q000737:chemistry*; D021281:Quantitative Structure-Activity Relationship; D043368:Ralstonia solanacearum / Q000187:drug effects* / Q000302:isolation & purification; D013450:Sulfones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014026:Nicotiana / Q000382:microbiology
chemical_list: D000900:Anti-Bacterial Agents; D010069:Oxadiazoles; D013450:Sulfones
keywords: 3D-QSAR; CoMFA; CoMSIA; antibacterial activities; sulfone derivatives; synthesis